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West Point Loma Boulevard, San Diego, CA, USA
Priced too high to cash-flow with a loan — an equity or tax play, not income.
Investment potential
Your scenario · adjust the levers below or open advanced settings to see how returns change
$97,599
$8,133/mo · at 64% occupancy & $601/night
-$69,596
-$5,800/mo after costs & mortgage
Cap rate
1.8%
Cash-on-cash
-15.3%
DSCR
0.30
Confidence
Your assumptions
Revenue
$97,599/yr
Market avg: $97,599/yr · 64% occ · $601 ADR
Financing
$100,019/yr
Operating costs
$67,176/yr
How this property compares to similar short-term rentals nearby.
Comparable set · 50 properties
$333–$912
Median $600
37%–93%
Median 65%
$57.7K–$209.2K
Median $92.5K
158–365
Median 275
This property · $97.6K
Comparable properties (50)
Cash flow potential Low · Appreciation potential Medium
324 days available · 288 days booked ·
358 days available · 304 days booked ·
261 days available · 210 days booked ·
313 days available · 224 days booked ·
365 days available · 171 days booked ·
275 days available · 177 days booked ·
273 days available · 171 days booked ·
325 days available · 146 days booked ·
319 days available · 222 days booked ·
235 days available · 150 days booked ·
263 days available · 154 days booked ·
277 days available · 210 days booked ·
313 days available · 145 days booked ·
324 days available · 172 days booked ·
278 days available · 168 days booked ·
292 days available · 150 days booked ·
265 days available · 160 days booked ·
317 days available · 145 days booked ·
237 days available · 142 days booked ·
221 days available · 154 days booked ·
172 days available · 123 days booked ·
182 days available · 153 days booked ·
215 days available · 157 days booked ·
365 days available · 274 days booked ·
216 days available · 146 days booked ·
250 days available · 128 days booked ·
356 days available · 213 days booked ·
282 days available · 175 days booked ·
231 days available · 178 days booked ·
288 days available · 160 days booked ·
262 days available · 155 days booked ·
216 days available · 175 days booked ·
275 days available · 130 days booked ·
240 days available · 104 days booked ·
322 days available · 158 days booked ·
320 days available · 148 days booked ·
259 days available · 136 days booked ·
278 days available · 119 days booked ·
290 days available · 148 days booked ·
237 days available · 116 days booked ·
248 days available · 124 days booked ·
307 days available · 179 days booked ·
260 days available · 132 days booked ·
290 days available · 140 days booked ·
304 days available · 196 days booked ·
257 days available · 122 days booked ·
293 days available · 160 days booked ·
158 days available · 128 days booked ·
234 days available · 151 days booked ·
268 days available · 98 days booked ·
Revenue and occupancy reflect Chalet's modeled estimates from observed booking activity for comparable active listings. Individual results vary with management, seasonality, and pricing.
Who this property is for
The same property is a great buy for one investor and a trap for another. Here's the honest read.
1031 / high-equity buyer
~$412.6K
Year-1 tax shield
Buying with cash or low leverage removes the debt-coverage problem entirely, so the thesis rests on appreciation plus a large first-year write-off. At roughly 25% of purchase price, the shield is substantial enough to carry the deal on its own.
Price-disciplined buyer
—
Break-even purchase price
Even a deep discount doesn't get this deal to break even within a realistic range, so there's no price anchor to negotiate toward. A price-disciplined buyer should pass unless the revenue assumptions change.
DSCR cash-flow buyer
0.30
DSCR at asking
At asking price the property doesn't cover its own debt service, so it won't qualify for DSCR financing as modeled. If you need cash flow from day one, look at a mid-term-rental fallback or a different San Diego submarket.
For a buyer who materially participates and qualifies for the STR tax treatment.
$412.6K
Estimated first-year deduction · range $342.4K–$470.4K
Why this matters here
At a marginal bracket, this deduction can be worth $126.7K–$174.0K in estimated federal tax saved.
This only applies if you meet the IRS material-participation tests for short-term rentals and are not using a full-service property manager.
Estimate, subject to CPA review. Cost-segregation percentages shown here are illustrative and depend on an actual study of the property.
California does not conform to federal bonus depreciation, so your state tax treatment will differ from the federal figures above.
Chalet can introduce a cost-segregation partner — this is not tax, legal, or financial advice.
How cash-on-cash return moves with purchase price. The marked line is break-even (1.0 DSCR).
At this price: cash-on-cash -15.3%, DSCR 0.30, cash flow -$69,596/yr
| Price vs asking | Price | Cash-on-cash | DSCR | Band |
|---|---|---|---|---|
| -25% | $1,252,800 | -12.9% | 0.41 | Below break-even |
| -22% | $1,302,912 | -13.3% | 0.39 | Below break-even |
| -15% | $1,419,840 | -14.0% | 0.36 | Below break-even |
| -8% | $1,536,768 | -14.7% | 0.33 | Below break-even |
| Asking | $1,670,400 | -15.3% | 0.30 | Below break-even |
| +8% | $1,804,032 | -15.9% | 0.28 | Below break-even |
| +15% | $1,920,960 | -16.3% | 0.26 | Below break-even |
Break-even price
Out of range
This deal does not reach break-even within ±25% of asking.
Discount needed
—
The gap between asking and the price a cash-flow buyer can underwrite.
If refi to 5.5% in 24 mo
+$14,660/yr
Illustrative cash-flow improvement at asking price if rates fall. Planning figure, not a forecast.
Annual avg $8,133 · peaks at $11,745 in Jul
Annual avg 60% · peaks at 82% in Jul
−$5,800/mo after all expenses
Cash to close
Down payment, closing costs, and furnishing
$484,416
Return on cash:2.9%
DSCR below 1.0 — but you can still qualify
Your DSCR is 0.3 · lenders typically require 1.0+.
Get matched with 2–3 vetted STR lenders, free.
What the deal returns over the hold — including the tax shield, which is the whole point for an appreciation buyer.
Levered IRR
5.8%
over 5-yr hold, with tax shield
Equity multiple
1.3×
total proceeds vs. $484,416 invested
Projected value at exit
$2,131,901
year 5 · 5.0% annual appreciation
Tax shield contribution
+5.5 pts
of IRR comes from year-1 depreciation
| Year | Equity | Appreciation | Cumulative cash flow | Total value |
|---|---|---|---|---|
| Year 1 | $430,326 | $83,520 | $83,062 | $596,908 |
| Year 2 | $443,972 | $171,216 | $14,930 | $630,118 |
| Year 3 | $458,605 | $263,297 | -$51,716 | $670,185 |
| Year 4 | $474,295 | $359,982 | -$116,854 | $717,422 |
| Year 5 | $491,119 | $461,501 | -$180,461 | $772,159 |
Projection, not a promise.
Assumes 5.0% annual appreciation, 1.5% rent growth (operating costs held flat), and that the property qualifies for short-term-rental tax treatment. The year-1 depreciation shield depends on a real cost-segregation study and your tax situation — consult a CPA.
Appreciation is the dominant driver of this return. When cash flow is negative, the deal depends on the property gaining value — it is not paying for itself from income.
Appreciation, rent growth, and financing rates are editable under Edit financials.
STR deals turn on local rules and demand that a generalist agent misses. Chalet matches you with a vetted San Diego agent who knows which properties actually cash flow — and which to avoid.
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Real Estate Investment Analysis & Market Insights
Disclaimer
This page and the data presented are for informational purposes only. The information provided should not be construed as financial, legal, or investment advice. Market conditions can change rapidly, and past performance does not guarantee future results. Always consult with qualified professionals before making investment decisions.
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